PornPorn Transgender • US
  • Videos
  • Short videos
  • photos
  • Users
    Forgot password
    Sign in with Google
    Sign in with X
    Sign up for free
    Home
    Live Sex
    Faphouse
    Premium Videos
    Categories
    Pornstars
    Channels
    Photos
    • Upload
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • Shemale Fucks Girl
    • Sissy
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Big Black Cock
    • Cum In Mouth
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Boyfriend Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    You switched to shemale orientation. Do you want to keep searching in the straight section?
    Sissy
    Boyfriend
    My Sissy Boyfriend
    Sissy Boyfriend Strapon
    Sissy Boyfriend Training
    Sissy Crossdresser and Boyfriend
    Asian Sissy and Boyfriend
    Passionate Sissy Fucked Boyfriend
    Fucking a Sissy Cheating Boyfriend
    From Boyfriend to Sissy Boyfriend
    Woman Turns Boyfriend Into Sissy Slave
    Femdom Anal Training for Sissy Boyfriend
    Sissy and Her Boyfriend Enjoying Sex
    Sissy Crossdresser
    Sissy Feminization
    Sissy BBC
    Sissy Chastity
    Sissy Husband
    Sissy Compilation
    Sissy Fucked
    Best Videos
    By clicking the content you will also see an ad. AD
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3.1M views
    My Sissy Boyfriend 07
    18:22
    My Sissy Boyfriend 07
    410K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    FapHouse
    2.2M views
    My Sissy Boyfriend 23
    19:43
    My Sissy Boyfriend 23
    205.7K views
    shemale dresses sissy to fuck
    16:14
    shemale dresses sissy to fuck
    2.1M views
    Lara Page sissy boyfriend
    15:47
    Lara Page sissy boyfriend
    95.6K views
    How to Train Your Sissy Boyfriend
    08:12
    How to Train Your Sissy Boyfriend
    FapHouse
    127.5K views
    Tgirl dominates her sissy boyfriend
    06:01
    Tgirl dominates her sissy boyfriend
    Transsensual
    103K views
    My Friend Sabrina and I Fucked the Boss Non-stop and with Great Desire.
    10:09
    My Friend Sabrina and I Fucked the Boss Non-stop and with Great Desire.
    FapHouse
    1.1M views
    My Sissy Boyfriend 22
    17:37
    My Sissy Boyfriend 22
    46.7K views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.3M views
    Sissy Boyfriend Sex Denial
    03:45
    Sissy Boyfriend Sex Denial
    FapHouse
    2.8K views
    I turned my straight roommate intro trans wife
    05:20
    I turned my straight roommate intro trans wife
    linktree
    553.3K views
    Ebony shemale  fuck sissy boyfriend
    22:33
    Ebony shemale fuck sissy boyfriend
    216.3K views
    Taking a straight guy home to turn him into my faggot - Elizabeth Stewart
    08:16
    Taking a straight guy home to turn him into my faggot - Elizabeth Stewart
    Elizabeth Stewart
    425.5K views
    Girlfriend Sissy Boyfriend to Go on Date With Man
    00:21
    Girlfriend Sissy Boyfriend to Go on Date With Man
    Onlyfans
    21.8K views
    dominant stepmom helps out her sissy slave
    05:59
    dominant stepmom helps out her sissy slave
    Pure Ts
    393.6K views
    CD TRAP SISSY EDUCATION TRAINING 101
    01:27:33
    CD TRAP SISSY EDUCATION TRAINING 101
    948.9K views
    Sissyfication
    43:09
    Sissyfication
    1.1M views
    family fun 1.mp4
    13:05
    family fun 1.mp4
    1.8M views

    Relevant Short videos

    Bangladeshi Cuckold Sissy Boyfriend fucking his ass with wooden dildo
    Bangladeshi Cuckold Sissy Boyfriend fucking his ass with wooden dildo
    CrossyBoudi
    101 views
    Sissy Boyfriend Sex Denial
    Sissy Boyfriend Sex Denial
    FapHouse
    209 views
    How to Train Your Sissy Boyfriend
    How to Train Your Sissy Boyfriend
    FapHouse
    327 views
    Ridin Boyfriend cock
    Ridin Boyfriend cock
    5K views
    Epic moment from "Rileydix treats stepson and boyfriends to her pussy!🩷"
    Epic moment from "Rileydix treats stepson and boyfriends to her pussy!🩷"
    RileyDix
    1.7K views
    Epic moment from "Shemale- My friend's boyfriend fucks me with his huge cock"
    Epic moment from "Shemale- My friend's boyfriend fucks me with his huge cock"
    FapHouse
    1.7K views
    Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    307.9K views
    He filled my ass with it, his drips a lot
    07:53
    He filled my ass with it, his drips a lot
    Piou_Sissy
    304.8K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    FapHouse
    867.3K views
    My step sister turned me into her trans wife
    05:13
    My step sister turned me into her trans wife
    linktree
    119.5K views
    Tv is for Sissies (Full Video)
    56:35
    Tv is for Sissies (Full Video)
    634.1K views
    Russian shemale fucks cute guy
    13:26
    Russian shemale fucks cute guy
    Shemale-Kitty
    1.4M views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.7M views
    Ultimate cuckold tranny humiliation!
    05:36
    Ultimate cuckold tranny humiliation!
    FapHouse
    82.7K views
    Male to female gender transformation smoking whore
    16:00
    Male to female gender transformation smoking whore
    709.8K views
    You Have to See What These Three Trans Women Did with This Hottie After the Party.
    22:24
    You Have to See What These Three Trans Women Did with This Hottie After the Party.
    FapHouse
    617.7K views
    Sissy Femboy Fucked From Behind
    05:20
    Sissy Femboy Fucked From Behind
    2.8M views
    My Slutty Step Sister: Kayleigh Coxx Uses Step Sister's Boy Toy Corbin Dallas
    11:12
    My Slutty Step Sister: Kayleigh Coxx Uses Step Sister's Boy Toy Corbin Dallas
    FapHouse
    112.6K views
    My stepmom is a tranny
    16:46
    My stepmom is a tranny
    FapHouse
    1.2M views
    Sensual Fist and Pegging Day with a French Stunning Trans Woman
    08:01
    Sensual Fist and Pegging Day with a French Stunning Trans Woman
    FapHouse
    141.7K views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    2.1M views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    2M views
    Never Expecting to Be a Sexy Girl
    08:12
    Never Expecting to Be a Sexy Girl
    Pure Ts
    499.9K views
    Sissy tranny fucks cute guy
    30:42
    Sissy tranny fucks cute guy
    Shemale-Kitty
    2.1M views
    Sexy Trans Girl Tricks Straight Boy and Fucks His Holes
    08:12
    Sexy Trans Girl Tricks Straight Boy and Fucks His Holes
    FapHouse
    311.6K views
    Sissy Joyce - A real life sissy slave
    01:16
    Sissy Joyce - A real life sissy slave
    FapHouse
    707.4K views
    Warning : Sissyfication is real - Sissy Joyce's warning
    03:57
    Warning : Sissyfication is real - Sissy Joyce's warning
    Onlyfans
    859.8K views
    Russian transsexual home video.  Shemale Fucks Young Guy In
    19:40
    Russian transsexual home video. Shemale Fucks Young Guy In
    Shemale-Kitty
    2.2M views
    Pounding My Boy Into Submission
    03:29
    Pounding My Boy Into Submission
    Elizabeth Stewart
    248.5K views
    The TS Fucked Deco Tlover's Mouth and Ass Mercilessly. He Had Double Penetration
    08:12
    The TS Fucked Deco Tlover's Mouth and Ass Mercilessly. He Had Double Penetration
    FapHouse
    479.8K views
    Sloppy blowjob and intense penetration with a FRENCH trans goddess
    08:36
    Sloppy blowjob and intense penetration with a FRENCH trans goddess
    Maxime horns
    203.6K views
    Sissy Slut Motel
    58:39
    Sissy Slut Motel
    741.8K views
    Rented Out by His Mistress
    06:12
    Rented Out by His Mistress
    Pure Ts
    88.6K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Boyfriend

    • Beautiful Sissy Boy
    • Secret Sissyboy
    • Crossdresser First Time With a Man
    • Femboy Fucks Guy
    • Cute Traps for Straight Guys
    • Dominant Shemale Male Submissive
    • Feminine Boys
    • Femboys Fucking
    • Feminized and Fucked
    • Please Fuck Me
    • Extreme Homemade
    • Transgender Twink
    • Slutty Nasty Crossdressing Gurl
    • Very Girly Ladyboys
    • Ruined
    • Giving Him an Experience
    • Femboygirlfriend
    • Sheboy
    • My Slut
    • Too Tight
    xHamster
    • Press
    • Blog
    • Creator's Blog
    • Advertising
    • xHamster Awards 2025
    Help
    • FAQ
    • Contact us
    • Content Removal
    • Improve xHamster
    Legal
    • Terms of use
    • Privacy policy
    • Cookies policy
    • DMCA/Copyright
    • Parental Controls
    • EU DSA
    • Trust and Safety
    Start making money with us
    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    Monetize your content
    Become a creator
    © 2007 - 2026, xHamster.com
    Mobile Version
    18 U.S.C. 2257 Record-Keeping Requirements Compliance Statement
    RTA Restricted To AdultsRTA Restricted To Adults
    xHamster is adults only website!

    The content available on xHamster may contain pornographic materials.

    xHamster is strictly limited to those over 18 or of legal age in your jurisdiction, whichever is greater.

    One of our core goals is to help parents restrict access to xHamster for minors, so we have ensured that xHamster is, and remains, fully compliant with the RTA (Restricted to Adults) code. This means that all access to the site can be blocked by simple parental control tools. It is important that responsible parents and guardians take the necessary steps to prevent minors from accessing unsuitable content online, especially age-restricted content.

    Anyone with a minor in their household or under their supervision should implement basic parental control protections, including computer hardware and device settings, software installation, or ISP filtering services, to block your minors from accessing inappropriate content.

    To enter xHamster you must be 18 or older
    how to protect your minors
    RTA Restricted To AdultsRTA Restricted To Adults